About Us

Trailblazer Technology is a community of insurance technology veterans with a deep history of success building cloud solutions for the insurance industry.
At Trailblazer, we recruit people who think of the work they do as an important part of their identity. We’re so excited about delivering an exceptional result for our customers that extra effort doesn’t feel, well… doesn’t feel like “extra.”

Trailblazers Are Deeply Experienced Insurtech Experts:

Aaron Shapiro

Aaron Shapiro

President / CEO

Aaron is a globally recognized insurance technology executive with a long history of building world-class Insurtech companies focused on customer success. He has spent more than two decades advancing the state-of-the-art in insurance technology. Prior to founding Trailblazer Technology, Aaron served on the board of directors for Origami Risk and Gradient AI, led the growth of multiple organizations from early stage startups into large scale success. Like all Trailblazers, Aaron brings to bear a deep understanding of the complex business needs of insurance professionals and a long track record of delivering world class technology solutions.


Tracey Glass

Software Engineer & Product Manager

Tracey is a Software Engineer and Product Manager at Trailblazer Technology with a decade of insurance technology expertise. Tracey’s experience spans software development and systems implementation providing her a depth of understanding of our customers’ needs along with the technology skills to deliver best-in-class solutions. Prior to Trailblazer, Tracey held software development and systems implementation roles at Socotra, Britecore and USAA.


Steve Haney

Senior Software Engineer

Steve is a Senior Software Engineer at Trailblazer Technology. He is a skilled insurance technology expert with two decades of expertise in delivering innovative technology solutions to clients. His experience includes software development, product management, technology consulting, and a strong track record of building and managing successful teams. Prior to Trailblazer, Steve served in leadership roles at Origami Risk and Riskonnect’s Clearsight (formerly CS-STARS).

Brad Krawczyk (1)

Brad Krawczyk

Senior Solutions Architect

Brad is a Senior Solutions Architect at Trailblazer Technology who is a quality-driven and dynamic professional with over 15 years of experience.  His greatest successes are based on excellence in customer service delivery, process automation, workflow optimization, and product implementation.  Prior to Trailblazer, Brad has served in leadership and delivery roles at Origami Risk and Riskonnect’s Clearsight (formerly Marsh’s CS STARS).


Richard Mathis

Senior Software Architect

Richard is a Senior Software Architect at Trailblazer Technology with two decades of bringing business solutions from simple concepts to polished solutions. Prior to Trailblazer, Richard was the CTO of Insurium (formerly CHSI).

Jeremy Moore

Jeremy Moore

Senior Software Engineer

Jeremy is a Senior Software Engineer at Trailblazer Technology. He has two decades of experience designing and building large, scalable Web applications in private and government sectors including insurance, financial, and health.  His vast background brings innovative, client-focused solutions to software products reaching a global userbase.  Prior to Trailblazer, Jeremy served as a lead engineer for IHS Markit (now part of S&P Global) and a senior engineer at Origami Risk.


Dustin Poland

Vice President of Sales

Dustin is Trailblazer Technology’s Vice President of Sales. Dustin is an industry veteran who began his career as a claims representative with Safeco over 20 years ago. For over a decade, he has solved enterprise technology needs across all aspects of the insurance vertical as a producer and as a manager of sales teams. Dustin’s experience in rating, management systems, core systems, predictive analytics, automation, compliance, accounting & commissions allow him to see through the eyes of our clients to help them deliver world class customer experience, drive efficiencies, and maximize growth & profitability. Prior to Trailblazer Dustin held sales and leadership roles with Vertafore, EZLynx, Gradient AI, AgentSync and Comulate. 

Jeremy Moore

Sam Wagner

Software Engineer

Sam is a Frontend Engineer at Trailblazer Technology. He specializes in building out frontend solutions, proving technical support, and an exceptional customer experience. Prior to Trailblazer, Sam served as a Senior Consultant for Booz Allen Hamilton and the National Geospatial Agency.

Trailblazer Technology Is Funded By True Insurtech Investment Experts ManchesterStory Group.

ManchesterStory is a venture capital firm with a specialty in partnering with market-leading companies in the InsurTech, sector. Decades of experience with high-growth companies means ManchesterStory has significant expertise identifying exceptional management teams with the vision and capacity to identify major problems and effectively scale their business.

Jason Gross

Head of Platform

Jason serves as VP and Head of Platform at ManchesterStory. Jason facilitates Trailblazer’s access to ManchesterStory’s network of Insurance company LPs and their vast array of Insurtech portfolio companies. Jason brings a wealth of insurance technology expertise and a deep network of expert relationships. Prior to ManchesterStory Jason lead IT, strategy and innovation efforts for two leading property and casualty insurance carriers.


Matt Kinley


Matt serves as a Director on Trailblazer’s Board. Matt is Founding Partner of ManchesterStory Group. Matt is an experienced venture capital investor with more than 25 years of lead investor experience during his tenure at ManchesterStory and Pappajohn Capital Resources. Matt has served on the board of many startups through emerging growth companies and has served as President of a public company. Matt has experience investing in more than 80 insurtech, fintech and healthtech companies during his career.